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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:02 UTC

Update Date

2020-05-01 16:43:57 UTC

HMDB ID

HMDB0002666

Secondary Accession Numbers

HMDB02666

Metabolite Identification

Common Name

Thiamine monophosphate

Description

Thiamine monophosphate, also known as thiamin phosphoric acid or TMP, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin while the phosphorylated derivatives are the active forms.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END


  Mrv1652305012018422D          

 22 23  0  0  0  0            999 V2000
    1.3791    0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0147    1.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791   -1.2786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921   -0.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2293   -1.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    0.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -0.0455    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047   -0.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293    0.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272   -0.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    0.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4154   -0.8203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -0.0357    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8052    0.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -0.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052   -1.2814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -0.0438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 15 16  2  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  0  0  0  0
 13  4  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  2  0  0  0  0
  1 18  1  0  0  0  0
 19  3  1  0  0  0  0
 21  6  1  0  0  0  0
M  CHG  1  16   1
M  END
> <DATABASE_ID>
HMDB0002666

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1

> <INCHI_KEY>
HZSAJDVWZRBGIF-UHFFFAOYSA-O

> <FORMULA>
C12H18N4O4PS

> <MOLECULAR_WEIGHT>
345.334

> <EXACT_MASS>
345.078637286

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5906471213632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-1.63

> <JCHEM_LOGP>
-5.696316403219863

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.712600648963036

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6589988406382288

> <JCHEM_PKA_STRONGEST_BASIC>
5.507552519532389

> <JCHEM_POLAR_SURFACE_AREA>
122.44

> <JCHEM_REFRACTIVITY>
84.27259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamin monophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  C   UNK     0       2.574   0.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.027   2.392   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.574  -2.387   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.572   0.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.905  -0.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.895  -2.387   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.235   0.686   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      -6.565  -0.085   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      -5.795  -1.415   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.895   0.686   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -7.331  -1.415   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.005   0.838   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.251  -0.067   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      -0.775  -1.531   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       0.765  -1.531   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.241  -0.067   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       5.236   0.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.903  -0.082   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.903  -1.622   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.236  -2.392   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       6.570  -1.622   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.570  -0.082   0.000  0.00  0.00           N+0
CONECT    1   16   18                                                       
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4    7                                                       
CONECT    6   21                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16    2                                                  
CONECT   13   12   14    4                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15    1                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19    1                                                  
CONECT   19   18   20    3                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    6                                                  
CONECT   22   17   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0002666
HETATM    1  C1  UNL     1      -6.279   2.595   0.632  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.942   1.936   0.382  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.776   2.558   0.581  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.598   1.970   0.295  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.540   0.709  -0.225  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.387   0.041  -0.735  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.524  -0.844  -0.049  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.042  -1.758   0.802  1.00  0.00           C  
HETATM    9  S1  UNL     1       0.315  -2.510   1.473  1.00  0.00           S  
HETATM   10  C7  UNL     1       1.564  -1.605   0.623  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.962  -1.752   0.950  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.104  -1.832   0.038  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.081  -0.534  -0.623  1.00  0.00           O  
HETATM   14  P1  UNL     1       5.545   0.216  -0.211  1.00  0.00           P  
HETATM   15  O2  UNL     1       6.547   0.325  -1.270  1.00  0.00           O  
HETATM   16  O3  UNL     1       5.162   1.831   0.315  1.00  0.00           O  
HETATM   17  O4  UNL     1       6.230  -0.513   1.173  1.00  0.00           O  
HETATM   18  C10 UNL     1       0.825  -0.782  -0.121  1.00  0.00           C  
HETATM   19  C11 UNL     1       1.483   0.091  -1.164  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.772   0.067  -0.427  1.00  0.00           C  
HETATM   21  N3  UNL     1      -3.758  -1.280  -0.966  1.00  0.00           N  
HETATM   22  N4  UNL     1      -4.924   0.676  -0.127  1.00  0.00           N  
HETATM   23  H1  UNL     1      -6.458   3.231  -0.313  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.297   3.271   1.473  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.045   1.829   0.646  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.700   2.521   0.493  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.546  -0.408  -1.779  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.667   0.938  -1.059  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.054  -2.001   1.083  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.157  -0.933   1.761  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.077  -2.667   1.660  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.100  -1.942   0.437  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.004  -2.638  -0.735  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.139   1.901   0.304  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.786  -0.043   1.951  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.914   0.962  -0.715  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.101  -0.546  -1.833  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.721   0.459  -1.945  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.878  -2.066  -0.289  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.628  -1.472  -1.979  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
CONECT    3    4
CONECT    4    5    5   26
CONECT    5    6   20
CONECT    6    7   27   28
CONECT    7    8    8   18
CONECT    8    9   29
CONECT    9   10
CONECT   10   11   18   18
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   34
CONECT   17   35
CONECT   18   19
CONECT   19   36   37   38
CONECT   20   21   22   22
CONECT   21   39   40
END

HMDB0002666
     RDKit          3D
Thiamine monophosphate
 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.2786    2.5952    0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9423    1.9355    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    2.5582    0.5813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    1.9701    0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400    0.7094   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872    0.0412   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243   -0.8445   -0.0486 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0420   -1.7577    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -2.5097    1.4727 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -1.6047    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9618   -1.7522    0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044   -1.8325    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815   -0.5342   -0.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5448    0.2157   -0.2109 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5470    0.3249   -1.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1620    1.8308    0.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -0.5130    1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.7825   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    0.0914   -1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724    0.0674   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7581   -1.2801   -0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.6761   -0.1271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4577    3.2312   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970    3.2713    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0452    1.8288    0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002    2.5206    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.4083   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666    0.9379   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -2.0007    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -0.9332    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.6667    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -1.9422    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -2.6376   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    1.9005    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.0434    1.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    0.9620   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009   -0.5455   -1.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    0.4592   -1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -2.0665   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -1.4723   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 10 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 18  7  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 21 39  1  0
 21 40  1  0
M  CHG  1   7   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate	ChEBI
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]thiazolium	ChEBI
Thiamin monophosphate	ChEBI
Thiamin phosphate	ChEBI
Thiamine phosphate	ChEBI
TMP	ChEBI
Vitamin b1 monophosphate	ChEBI
Vitamin b1 phosphate	ChEBI
2-[3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
2-[3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
2-[3-[(4-Azanyl-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphoric acid	Generator
Thiamin monophosphoric acid	Generator
Thiamin phosphoric acid	Generator
Thiamine phosphoric acid	Generator
Vitamin b1 monophosphoric acid	Generator
Vitamin b1 phosphoric acid	Generator
Thiamine monophosphoric acid	Generator
Thiamine phosphoester	HMDB
monoPhosphate, thiamine	HMDB
Phosphoester, thiamine	HMDB
ThP	HMDB
Thiamin-p	HMDB
Thiamine-pi	HMDB
Thiamine monophosphate	ChEBI

Chemical Formula

C₁₂H₁₈N₄O₄PS

Average Molecular Weight

345.334

Monoisotopic Molecular Weight

345.078637286

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium

Traditional Name

thiamin monophosphate

CAS Registry Number

495-23-8

SMILES

CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1

InChI Key

HZSAJDVWZRBGIF-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
4,5-disubstituted 1,3-thiazole
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Azole
Thiazole
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:9533 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Baker	172.533	30932474
[M+H]+	MetCCS_train_pos	169.709	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-5.7	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.66	ChemAxon
pKa (Strongest Basic)	5.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.27 m³·mol⁻¹	ChemAxon
Polarizability	32.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.891	30932474
DeepCCS	[M-H]-	160.533	30932474
DeepCCS	[M-2H]-	193.866	30932474
DeepCCS	[M+Na]+	169.094	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	174.5	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.29 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8389 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	495.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	368.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	215.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	65.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	307.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	261.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	943.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	556.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	45.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	582.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	627.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	435.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	466.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiamine monophosphate	CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	4050.4	Standard polar	33892256
Thiamine monophosphate	CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	2695.4	Standard non polar	33892256
Thiamine monophosphate	CC1=C(CCOP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	3039.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiamine monophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3030.8	Semi standard non polar	33892256
Thiamine monophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	2794.9	Standard non polar	33892256
Thiamine monophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	4508.1	Standard polar	33892256
Thiamine monophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3105.3	Semi standard non polar	33892256
Thiamine monophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	2756.8	Standard non polar	33892256
Thiamine monophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	4851.8	Standard polar	33892256
Thiamine monophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	2985.5	Semi standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	2876.4	Standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	4057.8	Standard polar	33892256
Thiamine monophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3042.1	Semi standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	2838.7	Standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	4078.0	Standard polar	33892256
Thiamine monophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3035.2	Semi standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2912.7	Standard non polar	33892256
Thiamine monophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	4404.7	Standard polar	33892256
Thiamine monophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3020.3	Semi standard non polar	33892256
Thiamine monophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	2912.1	Standard non polar	33892256
Thiamine monophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3621.6	Standard polar	33892256
Thiamine monophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3031.8	Semi standard non polar	33892256
Thiamine monophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2938.5	Standard non polar	33892256
Thiamine monophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3766.6	Standard polar	33892256
Thiamine monophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3039.3	Semi standard non polar	33892256
Thiamine monophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	2965.7	Standard non polar	33892256
Thiamine monophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3369.3	Standard polar	33892256
Thiamine monophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3269.3	Semi standard non polar	33892256
Thiamine monophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3010.0	Standard non polar	33892256
Thiamine monophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	4570.9	Standard polar	33892256
Thiamine monophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3320.4	Semi standard non polar	33892256
Thiamine monophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	2977.8	Standard non polar	33892256
Thiamine monophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4788.9	Standard polar	33892256
Thiamine monophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3428.0	Semi standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3254.3	Standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	4172.1	Standard polar	33892256
Thiamine monophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3455.9	Semi standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3233.8	Standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4175.1	Standard polar	33892256
Thiamine monophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3472.1	Semi standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3331.8	Standard non polar	33892256
Thiamine monophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4364.4	Standard polar	33892256
Thiamine monophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3603.9	Semi standard non polar	33892256
Thiamine monophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3429.3	Standard non polar	33892256
Thiamine monophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3858.1	Standard polar	33892256
Thiamine monophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3630.6	Semi standard non polar	33892256
Thiamine monophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3509.7	Standard non polar	33892256
Thiamine monophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3905.0	Standard polar	33892256
Thiamine monophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3784.7	Semi standard non polar	33892256
Thiamine monophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3634.1	Standard non polar	33892256
Thiamine monophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3655.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine monophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine monophosphate 35V, Positive-QTOF	splash10-00di-0900000000-113c390c4d19be64bd0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine monophosphate 40V, Positive-QTOF	splash10-00ec-9600000000-7ac71f27ba3ca0e2fe91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine monophosphate 10V, Positive-QTOF	splash10-00di-0900000000-3cf7f44d89518227c630	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine monophosphate 20V, Positive-QTOF	splash10-00di-1900000000-135b9e1aef14efaa6b3e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 10V, Positive-QTOF	splash10-0002-0109000000-eaecb343c9ff0c6f060f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 20V, Positive-QTOF	splash10-0002-9148000000-58b0f8616c541d910c2a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 40V, Positive-QTOF	splash10-0a4i-3900000000-cbb443e2c206edc550d7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 10V, Negative-QTOF	splash10-0006-4109000000-1d9d048d26c541eac8d6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 20V, Negative-QTOF	splash10-002b-9001000000-3b5f50e234444b8876e6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 40V, Negative-QTOF	splash10-004i-9000000000-8a23656944b47d54a23a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 10V, Positive-QTOF	splash10-006t-0519000000-8f42bf528fe96c321951	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 20V, Positive-QTOF	splash10-00di-0930000000-7ae879f5468ac7078781	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine monophosphate 40V, Positive-QTOF	splash10-00di-0900000000-b2954ab23477c3f8bdbc	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Mitochondria

Biospecimen Locations

Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Thiamine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0043 +/- 0.0024 uM	Adult (>18 years old)	Both	Normal	12111441	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0035 +/- 0.0038 uM	Adult (>18 years old)	Both	Alzheimer's disease	12111441	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Molina JA, Jimenez-Jimenez FJ, Hernanz A, Fernandez-Vivancos E, Medina S, de Bustos F, Gomez-Escalonilla C, Sayed Y: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. J Neural Transm (Vienna). 2002 Jul;109(7-8):1035-44. [PubMed:12111441 ]

Associated OMIM IDs

104300 (Alzheimer's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thiamine_monophosphate

METLIN ID

Not Available

PubChem Compound

1131

PDB ID

Not Available

ChEBI ID

9533

Food Biomarker Ontology

Not Available

VMH ID

THMMP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Tallaksen CM, Sande A, Bohmer T, Bell H, Karlsen J: Kinetics of thiamin and thiamin phosphate esters in human blood, plasma and urine after 50 mg intravenously or orally. Eur J Clin Pharmacol. 1993;44(1):73-8. [PubMed:8436160 ]
Kimura M, Itokawa Y: Determination of thiamine and its phosphate esters in human and rat blood by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1985 Sep 20;332:181-8. [PubMed:4055941 ]
Lu W, Kimball E, Rabinowitz JD: A high-performance liquid chromatography-tandem mass spectrometry method for quantitation of nitrogen-containing intracellular metabolites. J Am Soc Mass Spectrom. 2006 Jan;17(1):37-50. Epub 2005 Dec 15. [PubMed:16352439 ]
Tallaksen CM, Bohmer T, Bell H, Karlsen J: Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):127-36. [PubMed:1860908 ]
Tallaksen CM, Bell H, Bohmer T: Thiamin and thiamin phosphate ester deficiency assessed by high performance liquid chromatography in four clinical cases of Wernicke encephalopathy. Alcohol Clin Exp Res. 1993 Jun;17(3):712-6. [PubMed:8333605 ]
Tallaksen CM, Bohmer T, Bell H: Concentrations of the water-soluble vitamins thiamin, ascorbic acid, and folic acid in serum and cerebrospinal fluid of healthy individuals. Am J Clin Nutr. 1992 Sep;56(3):559-64. [PubMed:1503069 ]

Enzymes

Enzyme Details

1. Cancer-related nucleoside-triphosphatase

General function:: Involved in nucleotide binding
Specific function:: Has nucleotide phosphatase activity towards ATP, GTP, CTP, TTP and UTP. Hydrolyzes nucleoside diphosphates with lower efficiency.
Gene Name:: NTPCR
Uniprot ID:: Q9BSD7
Molecular weight:: 20712.935

Reactions

Thiamine pyrophosphate + Water → Thiamine monophosphate + Phosphate	details

Enzyme Details

2. 14 kDa phosphohistidine phosphatase

General function:: Involved in phosphohistidine phosphatase activity
Specific function:: Exhibits phosphohistidine phosphatase activity.
Gene Name:: PHPT1
Uniprot ID:: Q9NRX4
Molecular weight:: Not Available

Showing metabocard for Thiamine monophosphate (HMDB0002666)

MOL for HMDB0002666 (Thiamine monophosphate)

3D MOL for HMDB0002666 (Thiamine monophosphate)

3D SDF for HMDB0002666 (Thiamine monophosphate)

3D-SDF for HMDB0002666 (Thiamine monophosphate)

PDB for HMDB0002666 (Thiamine monophosphate)

3D PDB for HMDB0002666 (Thiamine monophosphate)

SMILES for HMDB0002666 (Thiamine monophosphate)

INCHI for HMDB0002666 (Thiamine monophosphate)

Structure for HMDB0002666 (Thiamine monophosphate)

3D Structure for HMDB0002666 (Thiamine monophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions